2, 6-bis (2-ethylhexyl) hexahydro-7-methyl-1h-imidazo [1, 5-c] imidazole and processfor its production



Unite 3,395,154 2,6 BIS(2 ETHYLHEXYDHEXAHYDRO 7- METHYL 1H IMlDAZO[1,5-e]IMIDAZOLE AND PRGCESS FOR ITS PRODUCTEON Freeman H. McMillan, Randolph Township, Dover, N.J., assignor to Warner-Lambert Pharmaceutical ompany, Morris Plains, N.J., a corporation of Delaware No Drawing. Continuation-impart of application Ser. No. 391,025, Aug. 20, 1964. This application Sept. 27, 1967, Ser. No. 671,147

4 Qlaims. (Cl. 260-3097) ABSTRAtIT OF THE DISDLGSURE A process for the production of 2,6-bis (Z-ethylhexyl) hexahydro-h-methyl-lH-imidazo[1,5-c] imidazole, by reacting 5-amino1,3-bis[Z-ethylhexyl] hexahydro-S-methylpyrimidine with formaldehyde. The compound so formed is useful as an anti-microbial agent.

This application is a continuation-in-part of my copending application Ser. No. 391,025, filed Aug. 20, 1964, now US. Patent 3,357,886.

This invention relates to a novel compound of the formula:

2 CH2 CH 0 11 which is available commercially as hexetidine, with an aqueous solution of formaldehyde Conveniently, the

aqueous formaldehyde of commerce containing about 37% formaldehyde can be employed. The reaction may be effected at reflux temperature with or without the use of a solvent. If solvents are employed, lower alkanols such as methanol, for example, are preferred. The desired final product is recovered from the reaction mixture by distillation under a vacuum.

The following example is included in order further to illustrate the process of this invention.

States Patent 0 "ice Example In a round bottom flask is placed 6.8 grams (0.02 mol) of hexetidine, 25 ml. of methanol and 1.62 grams (0.02 mol) of 37% aqueous formalin solution. The mixture is heated under reflux for 4 hours after which the solvent is removed under vacuum. The residue is distilled at oil pump vacuum to give 4.5 grams of 2,6-bis(2-ethylhexyl) hexahydro-7u-methyl 1H-imidazo[1,5-c]imidazole, boiling at /0.02 mm.

It is understood that the foregoing detailed description is given merely by way of illustration and that many variations may be made therein without departing from the spirit of my invention.

Having described my invention, What I desire to secure by Letters Patent is:

1. Process for the production of a compound of the formula:

which comprises contacting a compound of the formula:

C 11 with formaldehyde.

2. Process for the production of a compound of the formula:

CH3 HZC(IJ'CHZ O4H3OHCH2N N N-OHzCHCdI; 62H; oflz Cfiz 2H6 which comprises contacting a compound of the formula:

aC Cz s (IJHZCH(CH2):;CH3

with a solution containing 37% formaldehyde.

3. Process according to claim 2 wherein the reactants are employed at approximately equimolar ratio.

4. 2,6-bis(2-ethylhexyl)hexahydro 7a methyl-1H- imidazo [l,5-c]imidazole.

References Cited UNITED STATES PATENTS 2,393,826 1/1946 Senkus 260309.7 2,436,779 2/ 1948 Senkus 260-583 JOHN D. RANDOLPH, Primary Examiner.

N. TROUSOF, Assistant Examiner. 

